


The Miseducation of John Silver

by ElDiablito_SF



Series: SF Verse [2]
Category: Black Sails
Genre: Alternate Universe - Modern Setting, Explicit Sexual Content, Flint vs. Millennials, Gags, M/M, Spanking, hipster!Silver
Language: English
Status: Completed
Published: 2016-12-06
Updated: 2016-12-06
Packaged: 2018-09-06 21:45:18
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,218
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8770543
Author URL: https://archiveofourown.org/users/ElDiablito_SF/pseuds/ElDiablito_SF
Summary: After meeting Silver in that elevator incident, Flint decides to make more terrible life decisions which will make him regret everything of all time ever.  Probably.





	

**Author's Note:**

  * For [Craftnarok](https://archiveofourown.org/users/Craftnarok/gifts).



> A whole bunch of you encouraged this, but especially Laura <3\. So I hope you like! This is now an actual SF Verse!

There comes a time in a man’s life when he must face himself and admit the truth. James Flint took a long look at his reflection in the mirror of his office’s unisex bathroom and said, “I fucking hate you!” Then, he washed his hands.

It was inexplicable, really, why a man of proven intelligence would continually make his own life difficult. By choice.

“Good morning, Eleanor.” He nodded towards his named partner as he walked through the mahogany doors of Flint & Guthrie, LLP.

“Is it?” She lifted a dubious eyebrow at him.

“No, it most certainly is not.”

“We’re meeting a potential new client at 2 o’clock today!” she shouted after him, as he headed for his office and was about to put the blessed glass door between himself and the rest of San Francisco. “You will behave!”

Flint gave a noncommittal growl under his breath and paused. This was the perfect opportunity to give Eleanor some news of his own.

“I hired an intern,” he said.

“We can’t afford a fucking intern!” Eleanor nearly spilled her black coffee all over her pristinely white blouse. It was her power blouse; she always wore white to meet new clients. It made her look simultaneously confident and trustworthy. 

“Then it’s a good thing we’re not paying him,” Flint replied and finally slid the door closed. 

_No, really, James Flint, I fucking hate you,_ he informed himself as he took his seat at the desk and logged into his computer. What fresh hell awaited him today and how could it be any worse than yesterday? 

Yesterday, he thought life and fucking Universe had finally thrown him a bone in the form of a really pretty potential fucktoy who all but jumped him while they were stuck in the elevator. (Or perhaps it was Flint who had done most of the jumping… the memory was beginning to fade and become replaced by self-loathing and despair.) So then, why did he have to ruin what may have been a perfectly pleasurable hookup (especially if Silver was willing to entertain wearing a gag) by opening his mouth and saying, “I don’t want what happened between us to stand in the way of your career development.”

“You… don’t?” And there again, Flint was looking down a row of teeth so pearly they could barely be real. Silver moved a stray curl of hair out of his face. “What does that mean?”

“It means, if you want to interview for the internship, I’d still like to give you the opportunity to do so.”

“But surely, we can’t work together and...” The kid shook out his wild mane again, a soft aroma hitting Flint that he had recognized from the elevator. Coconut? Almond? The seductive piece of shit made himself smell like food on purpose, without doubt.

“Right,” Flint admitted, sourly. “We can’t _and_.”

“Because you’d be my boss.”

“A very astute observation.”

“That would be an HR nightmare, wouldn’t it?”

“You do realize I run a law firm, not a fast food stand, yes? I’m very well aware of the potential litigious implications of fucking an intern. Now, do you want the job or not?”

Simply replaying this conversation in his head, was making Flint want to throw his entire desk out the window. But with his luck, he’d actually squash a Facebook employee and get buried in lawsuits until the second coming of Christ. That is after he got disbarred.

“I do want the job,” Silver had said, still grinning and peeking up at Flint from under that dark canopy of eyelashes with his bright blue eyes. “But to be clear, I’m simply trying to decide which I want more. The job. Or to fuck you.”

“The job doesn’t pay,” Flint reminded him, hoping he’d put two and two together and make the smart choice. The way Silver was looking at his mouth left very little to the imagination. Flint was certain that his benevolent gesture would be noted by the Universe, bitcoin added to his Karma, as it were, and they’d immediately proceed to the nearest Uber to start pawing each other on the way back to Flint’s place. 

Which was why he crushed the coffee cup in his hand when Silver finally opened his mouth and said, “I’d love to intern in your office, Mr. Flint.”

It’s a good thing his coffee hadn’t been hot anymore. 

Flint ended up going home to change his pants before his next meeting, and stayed an extra fifteen minutes only to jerk off with as much indignation as he could muster at himself.

Obviously, the Universe was trying to punish him. He had been shit to Miranda when he left New York, their partnership, and her behind to come to San Francisco. He’d been shit about staying in touch. He would probably continue to be so until the anniversary of Thomas’ death rolled around again, at which time he might drunk dial her in the middle of the night, his mind and lips addled with booze and self-recrimination. If she’s lucky, with the time change, it will be morning by the time her phone rings. God, what a colossal asshole he was!

Flint’s inbox brimmed fifty new emails full and that was before nine o’clock. He hated the East Coast for having three hours on him. He hated the East Coast and he hated himself. Taking a deep breath, Flint dove into his emails. At least he could get some work done before the anthropomorphic representation of all his life’s bad decisions arrived at 11. 

***

“I picked up your lunch, Mr. Flint.” The curly one was beaming down at him, with an outstretched arm. Flint was glad at least one of them looked like he got rest that night, because he sure as shit didn’t sleep a wink, wondering how he was going to avoid becoming the embodiment of a sexual harassment lawsuit.

“Mm,” Flint replied, taking the phallic object out of Silver’s hand. “Did you complete your paperwork?”

“Yes, sir. It’s with Idelle.”

“You can call me James, you know. We’re not on TV. Colleagues don’t call each other Mr. Flint.” Flint avoided the kid’s eyes as he unwrapped the paper from around the _thing_ and beheld another layer of covering, this time black.

“Is that what we are now? Colleagues?”

“If you’re going to be a pain in my ass, you can turn around and go home before Idelle processes your volunteer package.”

“No, sir, James!” Silver saluted him. “I will not be a pain in your ass. Your ass and I are no longer on speaking terms, I thought I made myself quite clear yesterday when I chose this job.”

Flint bit his lips. _Don’t laugh. God’s sakes, don’t encourage him._ A small laugh of self-betrayal escaped him nevertheless. _Say something stern!_ “The fuck is this?”

“It’s a sushirrito.”

“The fuck did you just say?”

“A sushirrito! Come on, you’ve _heard_ of Sushirrito! We have three in the Financial District alone now! To be fair, I shouldn’t even go there anymore - it’s clearly gone mainstream. But their fish is responsibly sourced and they’re so delicious...”

“Do you ever say words that make sense to a person over 30?”

“Don’t be so hard on yourself, James, I’m sure you’re not that much over 30.”

Flint was going to punch this hipster prick. With his cock.

***

The sushirrito abomination turned out to just be a sushi roll the size and shape of a burrito. Fucking millennials and their portmanteaus! The worst part about the whole thing? Silver had been right: it _was_ delicious. And portable. Damn it. 

Silver had said he wanted the legal internship to make himself competitive for a law school scholarship. His LSAT score was surprisingly high for someone who traveled with a hip flask in his messenger bag. And apparently his grades from SF State had been more than respectable, if his resume didn't lie. But you weren’t going to be getting a full ride without some serious additional clout and a letter of recommendation from a well known civil rights law firm would certainly be a golden arrow in his quiver. The kid may not have been entirely a dumbass afterall, but he clearly still had a lot to learn, such as polite conversation and proper tie etiquette. 

His two o’clock with Eleanor and the mysterious new client approached at a rather martial pace. He threw his suit jacket back on, adjusted his matching tie, and tracked down Silver in the copy room with his arms full of still-warm papers.

“I need you to do something for me, John.”

“Woah, I thought we weren’t gonna…”

“Not _that_ kind of something!” Flint rolled his eyes and ran his hand through his hair. “Jesus, get over yourself, you’re not _that_ irresistible!”

“You corner me in the copy room…”

“Shut up.”

“Yes, sir.”

“This is real life, Silver, not a bloody porno.”

“I’m sorry. I understand.”

He may have said he understood, but again, the way Silver’s eyes lingered on Flint’s mouth conveyed anything but. Flint’s entire life was a vale of despair and frustration.

“As I was trying to say,” Flint cleared his throat, willing Silver to make eye contact with him. “Eleanor and I are meeting a potential new client in a few minutes. We’ll be in the conference room, behind Idelle’s desk. In about forty minutes, you’re going to walk by the conference room and look in. If my mobile is face up, I want you to walk in and make up an excuse to pull me out of that meeting. Make it sound really important. Do you think you can do that without embarrassing yourself and my company?”

“Yes,” Silver nodded, “absolutely. And if the phone is face down?”

“You keep walking. Am I clear?”

“Crystal.”

Flint smiled. This diversion was his own favorite power play. Eleanor had her white shirts; Flint liked to play different mindgames with his victims. Er… clients. As for Silver, he would either prove himself worth keeping, or be summarily dismissed and out of Flint’s life forever. 

***

Flint checked his watch. It was definitely time to close the deal. Neither he nor Eleanor were the kinds of people whose noses wouldn’t mind getting a bit of brown, and the new client looked exactly like the kind of guy who would have your lips surgically attached to his own asshole. He flipped his mobile face up, his thumb stroking anxiously at the screen. _Where the fuck is Silver?_

“Mr. Flint, a thousand pardons,” a curly head ducked into the conference room. Eleanor glanced over at Flint, a barely perceptible smile upon her lips. “I know you told me not to interrupt this meeting unless the building was on fire, except…”

“Is the building on fire?” Flint asked with mock sternness. He wondered if Silver could tell by the softness in his eyes that he was pleased with him. 

“This phone call is very important. I wouldn’t otherwise.” Silver glanced over at the megalomaniac seated across from them. “Really. _So_ sorry.”

“Out with it!” Flint spat at last.

“It’s Michelle Obama, sir.”

Both Flint and Eleanor rose from their seats. “Eleanor?” Flint glanced at his partner. “I must take this call. I regret to leave you both.”

“Of course, you go speak with the First Lady. I’ll wrap up our discussion here,” she replied with feigned benevolence. Her eyes spoke of impending victory. Eleanor was excellent at closing the deal.

Flint shook the man’s hand. What kind of name was Hornigold anyways? He really looked forward to charging Mr. RandyMoneybags his highest hourly rate.

Back in his own office, he locked the door and pushed Silver up against the desk, pressing his entire body alongside the young man’s until their noses all but touched. “Michelle Obama?”

“I can’t tell if you’re angry or just really horny,” Silver breathed out, his hands raised off the desk in a gesture of helpless surrender that Flint found all too irresistible.

“A bit of both, to be honest.” Flint leaned in and took the young man’s earlobe in between his teeth. 

“It worked, though? He thinks you hung the moon now,” Silver whimpered against Flint’s body. “Fuck…” His fingers dug into the folds of Flint’s blazer. “You know you send really mixed signals,” he protested, leaning into Flint and tilting his head backwards to allow easy access to his long, swanlike neck.

“How did you know he wasn’t a Republican?” Flint bit gently at the skin there, licking over the traces of his own teeth and loving the way Silver’s moan vibrated against the back of his throat.

“Would a Republican have picked a law firm known to specialize in civil rights violations and run by a partner who is on the list of Top Ten Gayest Attorneys in San Francisco?” Silver winked and leaned forward to capture Flint’s lip between his teeth. “You have to admit, that’s pretty gay.”

“You did your research?”

“I prepared for my interview.”

“You’re fired.”

“Hey!”

“I’m sorry,” Flint exhaled, pressing Silver bodily against the desk and letting his hands slide down his back until they rested on the pert globes of Silver’s likely Adonis-like ass. “It’s just that I’ll never survive with you working here. And I can’t very well come to work in a cock cage every day.” Silver raised a curious eyebrow. “Don’t even!”

“What about my brilliant, bright future?”

“I’ll write you a really _long_ letter of rec,” Flint sighed and fastened his lips upon the column of Silver’s neck, sucking the skin into his mouth, letting his teeth worry it just enough to make Silver keen softly and whimper against him.

“I like to actually earn my recommendations,” the saucy minx pronounced, even as his hand reached in between their bodies and cupped Flint’s balls in a firm grip.

“Oh, you _will_.”

***

“I never would’ve pegged you for a West Portal kind of guy,” Silver was announcing as Flint pushed him into his house. 

“I like West Portal.”

“It’s old fashioned.”

“I’m old.”

Silver laughed and threw his arms around Flint’s neck. “It’s quaint,” Silver admitted with a shrug. “But it’s definitely not…”

“If you say ‘mainstream’, I’ll gag you.” Silver wiggled his eyebrows and Flint attempted to hold them down with his thumbs. “You’re incorrigible.”

“Don’t incorrige me.”

“That’s it,” Flint said, pulling Silver towards the couch and then into his own lap, ass up. “That definitely deserves punishment.”

“You can’t fire me, I quit!”

Flint smacked Silver’s ass, which bounced and vibrated under his hand even through the tight-fitting material of his slacks.

“Oh, _fuck_. Thank you, sir, may I have another?”

Flint’s cock immediately rose to attention and he bit his own lip to keep a moan in that threatened to escape rather embarrassingly. He reached underneath Silver and undid the buckle of his belt, pulling it through the loops, and tossing it to the floor.

“Lower these,” Flint commanded, his voice dropping. Only too happy to oblige, Silver shimmied his slacks down his hips, pushing his briefs along with them. Yes, Flint was pleased he had not miscalculated this fine asset: Silver’s ass was perfectly round and so tight you could bounce a quarter off it. “Jesus,” Flint squeezed through gritted teeth and allowed one hand to trail over an exposed, pale globe.

“Are you going to sing it madrigals or…?”

Flint immediately remembered his original intent, and brought his open palm down upon Silver’s ass. It tightened appetizingly beneath his palm and Flint was rewarded with another soft moan of pleasure that dripped from Silver’s mouth. “Oh, god, yes!”

“You obviously need a firm hand, boy,” Flint said, slapping Silver again, loving the way the pale skin flushed a rapid pink under his palm. The rest of the kid’s skin was shockingly tan for Northern California, as if he’d spent the entire summer some place that had an actual summer. It reminded him what uncharted waters he was in with this John Silver personage.

“ _Fuck_ ,” Silver was beginning to drool onto Flint’s pant leg. Not to mention, likely make a whole other mess, judging by the way he rutted against his lap, his cock prodding and stabbing Flint angrily with each slap against his ass. Flint recalled with crystalline clarity what that gigantor felt like from their shared times in the elevator. His own cock gave a tortured twitch at the recollection. “Please… James.” His name, spoken in that little wrecked voice that Silver had suddenly acquired undid the last of Flint’s faculties.

“God damn it,” Flint spat out, shifting from underneath Silver but only to crawl over him and press his body deeper into the cushions of the couch with his own weight. It was a good thing the couch was leather. Although it was certainly not waterproof. “Why do I have no self control around you, you shit?”

“I believe,” Silver replied, pulling in his knees and sticking his ass out further against Flint’s weight, “the kids call it ‘chemistry,’ or so I’ve been told.”

Flint laughed despite himself, then reached to the floor, where Silver’s discarded belt lay in wait. He folded the leather straps against themselves and pulled Silver up by those longs curls, letting his fingers really sink in to get a solid grip. Silver gasped, his eyes pools of black surrounded by only the thinnest circle of bright cerulean.

“Bite on this,” Flint ordered, shoving the belt in between the mouthy kid’s teeth. Silver obeyed, as his nostrils flared and his eyelids lowered to half mast. Silver was painfully hard as Flint drew his lips down the sharp planes of his cheekbones. He let his teeth bite gently at the hinge of Silver’s jaw, along the stubble of his chin. “I knew you’d look good with a gag,” he muttered into the skin behind Silver’s ear, loving the way his body responded to each one of Flint’s touches with soft whimpers and shivers. 

He tore off the rest of Silver’s shirt and tossed it to the floor.

“I’m going to fuck you, boy.” Silver nodded enthusiastically and allowed his head to fall down over his folded arms, while his pinkened ass remained poised in mid-air, ready and beckoning. Flint couldn’t help but run his thumb along the cleft, until it came to rest against the hidden bud of Silver’s asshole. “Fuck, look at yourself. So good for me, now. Waiting patiently. I bet you could even take it dry, if I wanted you to.”

Silver moaned something unintelligible against the belt in his mouth.

“But don’t worry, you won’t have to take it dry,” Flint reassured, with another powerful slap against Silver’s ass. Flint was grateful to himself for having only one TV in his house, which forced him to keep extra lube in the living room, for, you know - all those times that a man gets the Friday night he deserves with a bottle of nice Spanish red wine and something fresh from the local Porn Palace. He quickly squirted some lube onto his fingers and returned his attention to Silver’s very laudable ass.

A flurry of attempted verbiage sank into leather and Flint smiled, taking his time, letting his fingers play and rub circles around Silver’s hole without breaching it. Silver bucked backwards in a valiant but futile attempt at impaling himself on Flint’s fingers.

“Hold still, or I won’t fuck you at all,” Flint threatened. His own cock, by then swollen and angrily crimson, gave Flint the stink eye for his own words. Silver keened against the belt and Flint grabbed him by the hair again, pulling until he could whisper into Silver’s ear as his mouth trailed up and down that taught, long neck. “You’d hate that, wouldn’t you? Not getting your way? You millennials are all so fucking entitled.”

At this, Silver angrily spat the belt out of his mouth. “Listen, old man…”

But Flint’s hand was there to stop him from speaking, and then his mouth had replaced it, kissing Silver deeply, letting his tongue explore the depth and breadth of Silver’s jaw. Their lips clung to each other with growing hunger, each one of their chests rumbled with a twin growl.

“You lost this,” Flint picked the belt up again and shoved it back between Silver’s teeth. “Really, darling. You look beautiful like this.” He punctuated this declaration with soft kisses peppered along the back of Silver’s neck and across his shoulder.

At last, his finger breached the tight ring he had been teasing, tearing another satisfied moan from Silver that got muffled by the leather bit.

“Such a good boy,” Flint whispered, probing, adding another finger and scissoring them inside Silver. He opened up so easily for him. “You’re going to feel so good. I can’t wait to be inside you.”

Flint suspected that whatever Silver had attempted to say was but another mouthful of sass. His ass thrusting against his lubricated fingers did all the talking Flint needed to hear, and he quickly lubed his cock up, poising it at Silver’s entrance.

“I know, baby. I’ll give you what you want.” His fingers slipped out, but he still held Silver’s ass spread open with his thumbs, lining his dripping cock up with Silver’s hole. “God damn it!” he suddenly remembered. 

“Mmm?”

“Condom. Jesus Fucking Christ, Silver! Were you seriously just going to let me fuck you bareback?”

“Mrrr?” Silver shrugged and wiggled his ass suggestively.

“How fucking stupid are you?”

Silver took the belt out of his mouth. “I’m on PrEP,” he announced.

“How do you know I don’t have herpes?”

“You really know how to be a boner killer, don’t you, Flint?”

Flint slapped his ass one more time, this time in actual ire, leaving an angry red handprint on him. He was certain he’d regret that later, yet Silver, somehow, didn’t seem particularly bothered. 

“I’ll be right back.”

His own cock, still rock hard, gave him a look of great disdain.

He came out of his bedroom, already sporting the condom. Silver’s eyes passed appreciatively over his body and Flint climbed back over him and pressed him once more into the couch.

“Can we please fucking get on with the fucking?” Silver asked and found Flint’s hand clasped over his lips again. The wet slide of his inhumanly long tongue along the palm of Flint’s hand was his only reply.

Silver’s body was so warm underneath Flint’s, his flesh simultaneously too soft and too hard. Flint burned with desire for him, a desire that he no longer could nor cared to rein in. He pulled back, once more taking Silver’s ass into his two hands and spreading him. His tight little asshole, still slick and stretched out, waited and winked at him. Flint pushed forward, at long last sinking his cock into the long-awaited tightness that swallowed him up.

“Oh, fuck, you feel so good,” Flint exhaled into the back of Silver’s neck. His hands came around and clawed at the tight muscles of Silver’s chest for purchase, his fingers grazed against the brown buds of Silver’s nipples causing the kid to moan and arch back into him, impaling himself fully on Flint’s cock. “Fucking _hell_ , you feel amazing.”

“Oh god, fucking split me in half, old man!” 

Right. He had forgotten to regag Silver’s big mouth. Flint didn’t give the remotest shit. Instead, he did as Silver requested, and put his weight into his hips, drilling his cock into Silver’s eager ass, over and over, until the room became filled with nothing but the sounds of flesh slapping against flesh and Silver’s incoherent fucked-out mutterings. When Flint’s own balls began to pull up, he reached underneath Silver and wrapped his fist around the shaft of his massive cock, squeezing and giving it a few sure strokes that were sufficient to send them both into erratic spasms. His lips were glued to the hair at the nape of Silver’s neck as Flint panted out the last jolts of his own orgasm and collapsed on top of Silver, allowing the sweat beading on his chest hair to mingle with the sweat pooling in the grooves of Silver’s vertebrae.

For a few minutes that may as well have been hours, they both floated in the blissful sea of post-coital silence. Flint’s cock heroically remained buried inside Silver, even in its deflated state. He was moved from his stupor by the sound of something buzzing annoyingly on the floor. Flint remembered he owned a phone. And a law firm.

He slid down the couch, using Silver’s ass as a pillow, as he picked up the phone and slid his thumb across the screen to answer.

“Eleanor?”

“I signed Hornigold,” his partner announced.

“Good for us,” Flint replied, attempting to keep his voice even. His pillow, in the meantime, was being oddly accommodating.

“What about you? Did you seal the deal?”

“That’s… I’ll…”

“Flint?”

“Yeah. I did.”

“Congratulations. I better not see him in the office tomorrow.”

The line went dead and Flint tossed the phone back onto the floor. Tomorrow was still many hours away. He turned his head and pressed a kiss to the inside of Silver’s thigh.

“Did I wear you out, young hipster?”

“You wish, grandpa!”

Oh yes. It was going to be a long night yet.


End file.
